NAV

2-Hydroxy-5-({1-[(4-Methylphenoxy)Methyl]-3-Oxoprop-1-Enyl}Amino)-L-Tyrosine

Identification

Generic Name
2-Hydroxy-5-({1-[(4-Methylphenoxy)Methyl]-3-Oxoprop-1-Enyl}Amino)-L-Tyrosine
DrugBank Accession Number
DB02537
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 386.3985
Monoisotopic: 386.147786446
Chemical Formula
C20H22N2O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhenylethylamine oxidaseNot AvailableArthrobacter globiformis
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phenylpropanoic acids / L-alpha-amino acids / Amphetamines and derivatives / p-Aminophenols / o-Aminophenols / Resorcinols / Phenoxy compounds / Phenol ethers / Aniline and substituted anilines
show 16 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Aldehyde / Alkyl aryl ether / Alpha,beta-unsaturated aldehyde / Alpha-amino acid / Amine / Amino acid / Aminophenol / Amphetamine or derivatives
show 33 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FSNBWEOGSXUNGF-CQMBDMNQSA-N
InChI
InChI=1S/C20H22N2O6/c1-12-2-4-15(5-3-12)28-11-14(6-7-23)22-17-9-13(8-16(21)20(26)27)18(24)10-19(17)25/h2-7,9-10,16,22,24-25H,8,11,21H2,1H3,(H,26,27)/b14-6+/t16-/m0/s1
IUPAC Name
(2S)-2-amino-3-(2,4-dihydroxy-5-{[(2E)-1-(4-methylphenoxy)-4-oxobut-2-en-2-yl]amino}phenyl)propanoic acid
SMILES
[H]\C(C=O)=C(\COC1=CC=C(C)C=C1)NC1=C(O)C=C(O)C(C[C@]([H])(N)C(O)=O)=C1

References

General References
Not Available
PubChem Compound
52941757
PubChem Substance
46509095
ChemSpider
26354103
ZINC
ZINC000103549492
PDBe Ligand
MBQ
PDB Entries
1sih

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0342 mg/mLALOGPS
logP-0.37ALOGPS
logP-0.67Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)1.69Chemaxon
pKa (Strongest Basic)8.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area142.11 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity106.02 m3·mol-1Chemaxon
Polarizability39.15 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5189
Blood Brain Barrier-0.9827
Caco-2 permeable-0.7553
P-glycoprotein substrateSubstrate0.7035
P-glycoprotein inhibitor INon-inhibitor0.8046
P-glycoprotein inhibitor IINon-inhibitor0.9057
Renal organic cation transporterNon-inhibitor0.9016
CYP450 2C9 substrateNon-substrate0.6676
CYP450 2D6 substrateNon-substrate0.8542
CYP450 3A4 substrateNon-substrate0.5998
CYP450 1A2 substrateNon-inhibitor0.5088
CYP450 2C9 inhibitorNon-inhibitor0.7051
CYP450 2D6 inhibitorNon-inhibitor0.8106
CYP450 2C19 inhibitorNon-inhibitor0.5764
CYP450 3A4 inhibitorNon-inhibitor0.8165
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6657
Ames testNon AMES toxic0.6473
CarcinogenicityNon-carcinogens0.9079
BiodegradationNot ready biodegradable0.7394
Rat acute toxicity2.0591 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.939
hERG inhibition (predictor II)Non-inhibitor0.865
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ac-0059000000-d0e03a2ddca27d2d7ab3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-0096000000-47e426bb52c1442c883c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-008c-0098000000-060b646d487f0363af90
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k9i-0290000000-043b790b432d87350cd6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9472000000-9ad263a78e28791c7c7c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-2951000000-75a73e474d414fcd9885
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.11427
predicted
DeepCCS 1.0 (2019)
[M+H]+193.50983
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.06123
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phenylethylamine oxidase
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P46881
Uniprot Name
Phenylethylamine oxidase
Molecular Weight
70645.405 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:43